DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride
Wang, Qiang; Xu, Jian; Xu, Zhou-Qing; Yan, Ji-Dan
2012-08-03 00:00:00
N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as 0.001 eq without reducing the efficiency of the chlorination. A plausible mechanism for the reaction was proposed and proved by experiments. The reaction is stereoselective and potentially chemoselective among primary benzyl alcohols, secondary benzyl alcohols, and unactivated aliphatic alcohols.
http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.pngResearch on Chemical IntermediatesSpringer Journalshttp://www.deepdyve.com/lp/springer-journals/dmso-catalyzed-chlorination-of-alcohols-using-n-phenylbenzimidoyl-Dvyx4kfk60